The first event took place in 1999, with the 3,000 mile journey starting in London, to Rimini, Italy and then back. Cooper planned different events on each night of the rally, ranging from parties to dinner events. The rally received coverage in the British media at the time as the rally and events surrounding The Gumball 3000 were attended by high-profile figures, such as Kate Moss and Guy Ritchie. The event commenced with a party at the Bluebird club in London. Cars that took place in this first rally included a British Police car borrowed from the British television show The Bill driven by Alexandra Aitken, a Lotus Esprit and a Lamborghini Diablo. Cooper made the decision not to use any form of timing or prizes for placed finishes in order to avoid criticism and promote safety.
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